(2-methyl-5-phenyloxazol-4-yl)(phenyl)methanone | 69163-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-methyl-5-phenyloxazol-4-yl)(phenyl)methanone
• 英文别名: 4-benzoyl-2-methyl-5-phenyloxazole；(2-methyl-5-phenyl-oxazol-4-yl)-phenyl-methanone；(2-methyl-5-phenyl-1,3-oxazol-4-yl)-phenylmethanone
• CAS: 69163-86-6
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: QFXXLQCWUPSPOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.1
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (Z)-N-(3-oxo-1,3-diphenylprop-1-en-2-yl)acetamide 在 碘苯二乙酸 、 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以76%的产率得到(2-methyl-5-phenyloxazol-4-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of Oxazoles from Enamides via Phenyliodine Diacetate-Mediated Intramolecular Oxidative Cyclization

  摘要：

  A group of functionalized oxazoles were synthesized in moderate to good yields from enamides via phenyliodine diacetate (PIDA)-mediated intramolecular cyclization. The main advantageous features of the present method include its broad substrate scope and the heavy-metal-free characteristic of the oxidative carbon-oxygen bond formation process.

  DOI：

  10.1021/jo302073e

文献信息

• Synthesis of Highly Substituted Oxazoles through Iodine(III)-Mediated Reactions of Ketones with Nitriles
  作者：Akio Saito、Nao Hyodo、Yuji Hanzawa

  DOI：10.3390/molecules170911046

  日期：——

  trifluoromethanesulfonic acid (TfOH) or bis(trifluoromethane-sulfonyl)imide (Tf2NH), iodosobenzene (PhI=O) efficiently promoted the reactions of dicarbonyl compounds as well as monocarbonyl compounds with nitriles to give 2,4-disubstituted and 2,4,5-trisubstituted oxazole in a single step under the mild conditions.

  在三氟甲磺酸 (TfOH) 或双（三氟甲磺酰基）酰亚胺 (Tf2NH) 存在下，碘代苯 (PhI=O) 有效地促进了二羰基化合物以及单羰基化合物与腈的反应，生成 2,4-二取代和 2 ,4,5-三取代恶唑在温和条件下一步完成。
• Three‐Component [2+2+1] Gold(I)‐Catalyzed Oxidative Generation of Fully Substituted 1,3‐Oxazoles Involving Internal Alkynes
  作者：Alexey Yu. Dubovtsev、Dmitry V. Dar'in、Vadim Yu. Kukushkin

  DOI：10.1002/adsc.201900097

  日期：2019.6.18

  Three‐component [2+2+1] gold(I)‐catalyzed reaction of internal alkynes (alkynyl esters or ‐ketones), nitriles, and 2‐chloropyridine N‐oxide led to a wide range of fully substituted 1,3‐oxazoles (32 examples; up to 92% isolated yields). Nitrile R3CN species, employed in the reaction as both reactants and solvents, comprise conventional nitriles (R3=Alk, Ar) and also push‐pull systems such as cyanamides

  三组分[2 + 2 + 1]金（I）催化内部炔烃（炔基酯或酮），腈和2-氯吡啶N-氧化物的反应，导致了各种各样的完全取代的1,3-恶唑（32个示例；高达92％的孤立产率）。反应中既用作反应物又作为溶剂的腈R 3 CN物种包括常规腈（R 3 = Alk，Ar）以及推挽式体系，如氰胺（R 3 = NH 2和NAlk 2）和硫氰酸酯（ R 3＝ SPr）。所开发方法的优点包括反应条件温和，官能团耐受性高，取代基R 1 / R 3范围广当R 1＝ NH 2时，还有可能容易修饰COR 2或氨基。
• THE BF₃CATALYZED DECOMPOSITION OF DIAZOCARBONYL COMPOUNDS IN NITRILES: SYNTHESIS OF OXAZOLES
  作者：Toshikazu Ibata、Ryohei Sato

  DOI：10.1246/cl.1978.1129

  日期：1978.10.5

  The BF3 catalyzed decomposition of diazocarbonyl compounds in nitriles afforded the corresponding oxazoles in high yield. This method is applicable to diazocarbonyl compounds such as m- and p-substituted diazoacetophenones, ethyl diazoacetate, azibenzil, dibenzoyldiazomethane, dimethyl diazomalonate, and 7-diazo-8-acenaphthenone.

  BF3 催化腈中重氮羰基化合物的分解以高产率提供相应的恶唑。该方法适用于重氮羰基化合物，如间位和对位取代的重氮苯乙酮、重氮乙酸乙酯、azibenzil、二苯甲酰重氮甲烷、重氮丙二酸二甲酯和7-重氮-8-苊酮。
• Photochemical three-component assembly of tri-substituted oxazoles through a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade
  作者：Xingchen Ye、Huaijin Pan、Yong Huang、Jiean Chen、Zhaofeng Wang

  DOI：10.1039/d4sc01355g

  日期：——

  synthesis. We report a novel visible-light-induced three-component reaction for the construction of complex 2,4,5-trisubstituted oxazoles, which are valuable in medicinal chemistry, from simple and readily available iodonium-phosphonium hybrid ylides, carboxylic acids, and nitriles. This reaction features a carbenic phosphorus-nitrile hybrid ylide formation/trapping cascade, in which a photo-generated α-phosphonium

  在有机合成中，利用普遍存在的化学原料在一次转化中构建复杂的分子骨架非常有吸引力。我们报告了一种新型可见光诱导的三组分反应，用于从简单且容易获得的碘鎓杂化叶立德、羧酸和腈构建复杂的2,4,5-三取代恶唑，这在药物化学中很有价值。该反应以碳磷-腈混合叶立德形成/捕获级联为特征，其中光生α-鏻卡宾充当序列触发器。这种无催化剂和无添加剂的转化表现出高效率和广泛的底物范围，可合成多种恶唑。
• IBATA I.; SATO R., CHEM. LETT., 1978, NO 10, 1129-1130
  作者：IBATA I.、 SATO R.

  DOI：——

  日期：——